tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-bromo-1,3-benzodioxol-5-yl)methyl)carbamate | 872831-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-bromo-1,3-benzodioxol-5-yl)methyl)carbamate
• 英文别名: tert-butyl N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-N-(2-phenylmethoxyethyl)carbamate
• CAS: 872831-98-6
• 化学式: C₂₂H₂₆BrNO₅
• 分子量: 464.356
• InChiKey: IFSXNIOUFNEWJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-((4R,5R)-5-((1-tert-butyl-1,1-dimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)vinyloxy](trimethyl)silane 、 tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-bromo-1,3-benzodioxol-5-yl)methyl)carbamate 在 二氯双(三邻甲苯膦)合钯(II) 、 三正丁基氟化锡 作用下， 以 苯 为溶剂， 反应 3.5h， 以52%的产率得到tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-[3-((4R,5R)-5-((1-tert-butyl-1,1-dimethylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxopropyl]-1,3-benzodioxol-5-yl)methyl) carbamate
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  2-苄基-1-乙胺 在 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 5.0h， 生成 tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-bromo-1,3-benzodioxol-5-yl)methyl)carbamate
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093